pick 5 101

For every three brackets (seats) you purchase as part of a bulk-rate package for a single participant, you'll receive one complimentary entry into the 2026 Pick 5 contest. Thus, 3-5 brackets will earn you a single Pick 5 entry, 6-8 brackets will earn you two Picks 5s, etc. You can't pay a fee to enter and you can't combine brackets from separate purchases (e.g. buying two brackets and adding a third a week later).

Pick 5 is simplicity itself: Beginning the evening of March 15 (Selection Sunday), pick any five teams in the field (if you choose a First Four team that loses, you can edit until 9:15 a.m. on March 19). For every win those teams produce, you'll receive the points that correlate to their seed #. For instance, if one of your teams is 6th-seeded Nebraska and the Huskers advance to the Elite Eight before being eliminated, you'll receive 18 points for their three wins (6 + 6 + 6).

And so on, for all five teams. Most points wins $1,000!

Take a look at the rosters of our first three Pick 5 winners:

There's no single formula for success. Our 2023 and 2025 winners chose conservatively; neither Nate Cressman nor Scot Donley had a seed higher than No. 6 on his Pick 5 roster. Auburn basketball alum Ty Cressman (Nate's son), on the other hand, captured the gold in 2024 by betting on three double-digit seeds.

Scot's winning roster scored less than half the points of either of the previous Pick 5 champs because 9 of the 10 most popular BreadHead picks in 2025 were eliminated by the completion of the second round. Despite his paltry total, Scot clinched his $1,000 during the Sweet 16 round.

While there's no proven path to the money, here's a pro tip: Think twice before picking a No. 1 seed ; even if a top seed runs the table, you'll reap just 6 points. Then again, any points beats 0 for a team that fails to win a game.